


Kinktober 2018: Simon

by CatherineMorgenstern



Series: Kinktober 2018 [8]
Category: The Walking Dead & Related Fandoms, The Walking Dead (TV)
Genre: (another couple joins unexpectedly and the dude gets blown while watching Simon take you), Come Swallowing, Cunnilingus, Deepthroating, Dirty Talk, Doggy Style, F/M, Fellatio, Flirting, Innuendo, Mutual Masturbation, Simon likes being watched, Vaginal Fingering, Wall Sex, dominant Simon, no penetrative sex in chapter two, some light groping, turns out you like watching, unprotected sex (wrap it up kids)
Language: English
Status: Completed
Published: 2018-10-12
Updated: 2018-10-17
Packaged: 2019-08-01 03:32:29
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 5,658
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16276994
Author URL: https://archiveofourown.org/users/CatherineMorgenstern/pseuds/CatherineMorgenstern
Summary: Little Red:The Sanctuary is aflutter with a wicked Halloween party and Simon's Michael Myers’ mask does all kinds of funny things to you.Desire:Having had your eye on Simon for a while, you decide it's time to seduce the man.*Warnings for each chapter inside*





	1. Little Red

**Author's Note:**

> As always, a big smooch to my super supportive beta, [Heeley](https://archiveofourown.org/users/Heeley/pseuds/Heeley).

**Summary for the Chapter:**

> The Sanctuary is aflutter with a wicked Halloween party and Simon's Michael Myers’ mask does all kinds of funny things to you.
> 
> Warnings: some light groping, sex against a wall, doggy style, unprotected sex (wrap it up, kids), Simon likes being watched and it turns out you like watching (another couple joins unexpectedly and the dude gets blown while watching Simon take you)

**Day 12 of Kinktober:** ~~Licking~~ | ~~Pet Play~~ | ~~Rimming/Analingus~~ | **Costume**

* * *

The Sanctuary's interior was illuminated by red light that was just bright enough not to stumble into anything but dim enough that it looked sufficiently creepy. The noise of rain pelting the windows and wind howling through trees with rustling leaves echoed off the cement walls even though you knew for a fact that it was still sunny outside.

 

You were on your way to the Halloween party Negan had decided to throw. And even though you were one of his Saviors and killed Walkers on a daily basis, you couldn't deny that the atmosphere made you a little jumpy. Maybe it was because you hadn't been responsible for decorating this place so you hadn't known what to expect.

 

Your job had been to help with costumes. Best case scenario would've been to find an abandoned costume shop that hadn't been raided but you hadn't been that lucky. Instead you'd made sure to raid all closets of any house you passed by in order to provide the Sanctuary with clothes that could be made into costumes and, as luck would have it, you'd come across a short, red cape that you'd instantly snatched for yourself. Perks of being a Savior. While everyone had to work for points and nothing was given freely, you did get first dibs and you'd instantly decided to go as Little Red Riding Hood when you'd seen it. After convincing Frankie to lend you one of her longer (as in below the knee), flowing dresses and a pair of high heels, you'd borrowed an apron from the kitchen and got white socks from Commissary. With your hair in pigtails and a touch of make-up, your outfit was all done.

 

Already, you could hear music and laughter echo through the Sanctuary.

 

Narrowing your eyes at the corner ahead of you, you thought you'd behead anyone who dared jump out and try to scare you. Though you were wearing something comparatively innocent, it didn't mean you wouldn't retaliate if anyone got too forward. Naturally, you hadn't gone without weapons. A knife was strapped to your thigh while your gun holster was hidden perfectly by the heavy, velvet cape.

 

Better safe than sorry.

 

Teetering on the impossibly high heels - in your opinion anyway, they had actually been Frankie's lowest pair -, you rounded the corner.

 

A grin appeared on your face as you observed the different costumes - people could be really creative when they wanted to be - as you took stock of bed linens that had been formed into ghosts which were now hanging from the ceiling while pumpkins served as typical jack o'lanterns. The latter were strewn throughout the massive hall; you were a little concerned about the fire hazard they posed, hopefully no one would get drunk enough to knock them over. You made a mental note to not let that be you.

 

Negan's booming laughter was recognisable over the pulsing music. You strolled closer while keeping your eye peeled for Simon and Arat. The Sanctuary's leader was dressed as Dracula while his wives were made up as Dracula's brides. How fitting.

 

“Doll!” he exclaimed cheerfully, clapping his hands, when he noticed you. “My, don't yer look fuckin’ ravishin’? Maybe yer should reconsider becomin’ one of Dracula's fuckin’ brides. Huh, baby?”

 

Rolling your eyes at him, you smirked. “I think you got your hands full, oh evil one.”

 

“Nah,” he replied with a grin, “I’d make some goddamn space for 'lil Red any time.”

 

“Yeah?” you drawled provocatively. “Not too busy impaling your brides?”

 

Negan threw his head back and roared with laughter before leering at you. “Never, doll, but no one said yer can't make it a fuckin’ party of, say,  seven.”

 

“I think I'll pass,” you said, shaking your head at him and excused yourself when you spotted Arat.

 

You almost hadn't recognised her. She was dressed as Marilyn Monroe, which, truth be told, would've been the last costume you expected her to choose.

 

“You look awesome!” you screeched as you took her hands to inspect her properly.

 

“Thanks,” she mumbled gruffly before adding with a grimace, “I spent all day being fussed over by Amber.”

 

Laughing, you replied, “Well, it paid off. Have you had a drink yet?”

 

“No, but Laura's getting moonshine. Told her to get some for you as well.”

 

“Awesome, thank you. Though maybe we should grab something to eat before indulging in Dwighty-boy's concoction.”

 

“Probably, but where would the fun be in that?”

 

“Oooohhh, Arat,” you teased, bumping her shoulder with your fist, “someone's come to play!”

 

“Shut up,” she replied good-naturedly. “Did the boss hit on you?”

 

“It's Negan,” you said with a shrug. “He can't help himself. Has he seen you yet?”

 

Arat's cheeks tinged a light pink. “Yeah.”

 

“And?!”

 

“Nothing.”

 

“Oh, c'mon! Give me something!”

 

“Like you said, he's Negan, he can't help himself,” she murmured, looking uncomfortable with the attention.

 

Taking pity on your friend, you changed the subject. “Have you seen Simon yet?”

 

“No, but I'm sure he's around here somewhere,” she said with a frown before smirking at you deviously. “Why? Planning on finally resolving that unbearable sexual tension between you two?”

 

“What?” you squeaked before clearing your throat. “I have no idea what you're talking about.”

 

“Of course you don't. It's not like you're basically fucking each other with your eyes --.”

 

“Oh, look!” you interrupted. “There's Laura.”

 

“Hey,” Laura greeted you as she handed you a drink. “You look great. All innocent and sweet, remarkable how you manage to pull that off. Great acting.”

 

“Excuse me? Are you implying I'm not usually innocent and sweet?”

 

“Yup.”

 

“Bitch,” you said with a grin. “Or should I say witch? That outfit really suits you, though we should've put some warts on your face to reflect your pleasant personality.”

 

“Screw you,” Laura replied before clinking her glass to yours. “What were you guys talking about?”

 

“Nothing!”

 

“Oh, we were just looking for Simon…” Arat said, smirking evilly.

 

“Oh yeah?” Laura asked before giving you a side-eye. “You finally gonna fuck him?”

 

“Why is everyone assuming that?!”

 

Laura gave you a look. “Don't play dumb.”

 

You scoffed. “You've all lost it. Maybe the moonshine fumes got to you. And besides, if anyone's gonna fuck someone tonight it'll be Negan finally getting into Arat's non-existent pants.”

 

The woman in question choked on her drink as Laura cackled.

 

“Oh god, I hope so. I've put money on that ages ago.”

 

“You what?” Arat yelled, looking scandalised.

 

“Yeah, me too,” you joined in. “C'mon, Arat, take one for the team… even if it's rumoured to be a big one.”

 

“Fuck you. Both of you.”

 

You continued teasing each other as more and more Saviors joined your little circle, not missing how Laura kept eyeing Dwight appreciatively - which made you shudder a little - and before long you were rather drunk. That stupid moonshine really packed a punch so you and Laura finally hunted down some food. Weirdly enough, being inebriated made walking in these shoes much easier or maybe you'd just gotten accustomed to them and the alcohol was masking the pain.

 

Deciding to go to the restroom after you were fed and your head felt much clearer, you separated from Laura who went back towards the party. Once you were done, you cleaned up your makeup and straightened your pigtails.

 

On your way back, you thought you heard heavy footsteps following you through the deserted corridor and when you looked over your shoulder you saw a white mask in the dim light and what looked like a large knife floating next to it. Your heart rate accelerated as the eeriness of the situation raised goosebumps on your skin. For a second, you debated whether to simply run and then you thought that a) you'd probably break a leg trying to run in these death traps women called shoes, b) it was probably someone you knew playing a prank on you and c) if it wasn't, you were armed.

 

Your hand gripped your knife’s handle, sliding the first few inches out of its sheath as you turned around and faced your pursuer head on. As the mask drew nearer, you were able to make out black clothes and the way the man held himself was oddly familiar.

 

Cocking your head, you narrowed your eyes. “Simon?”

 

A deep chuckle could be heard as he came to stand in front of you that was slightly muffled by the mask. He reached up to slide the mask back onto his hair, revealing that unmistakable, ostentatious moustache, a wide grin and twinkling eyes.

 

“Ah, you got me, dove,” he said. “But I did make you reach for your knife!”

 

“You jerk!” you shrieked, swatting at him as you let go of your weapon after you'd secured it again.

 

“What? It's Halloween! It's supposed to be scary, right?”

 

“You didn't have to stalk me!”

 

“No, I didn't have to,” Simon agreed, “but I wanted to.”

 

“Just you wait, payback's a bitch.”

 

“Payback? What'cha gonna do? Scare me with your cutesy costume?”

 

“Shut up,” you hissed, “I might not be able to scare you but Christmas isn't that far away, Mr Grinch.”

 

Simon groaned. “Nooooo…”

 

“You have no one to blame but yourself,” you replied cheerfully in a singsong voice.

 

“I need a drink,” he grumbled

 

“C'mon then, everyone's been wondering where you were anyhow.”

 

“Everyone?” he repeated with a wicked smirk. “Or just you?”

 

“Oh my god, you're so full of yourself it's a wonder that mask even fits over your big head,” you retorted as you joined your group of friends. “Look who I've found hiding in the corridors like some weirdo.”

 

A chorus of hello's greeted Simon before both of you had a drink thrust into your hands. Arat and Laura shot you meaningful looks and you told them to shut the fuck up, making them laugh. A few hours later found you comfortably intoxicated and sitting on Simon's lap. You were giggling at the scene Laura was making as she kept grabbing Dwight's bum to Sherry's great displeasure while Arat stuttered every time Negan made a comment on her assets. The boss man kept eye fucking her even though he had his arms around two of his wives. You really hoped Arat was gonna tap that and not only because you liked to win; you were dying to hear if he was as good in bed as he liked to boast.

 

Simon's hand was creeping up your bare thigh, brushing over your knife and squeezing the flesh just above it before sliding even higher which brought his fingertips dangerously close to your cunt.

 

“How yer feelin’, dove?” he murmured into your ear.

 

“Just fine,” you replied, squirming a little. “How about you?”

 

“A little hot under the collar.”

 

“Oh yeah?”

 

“Yeah.”

 

Clicking your tongue, you drawled with faux innocence, “Whatever shall we do about that?”

 

“I got a few ideas I could use yer help with,” he growled.

 

“That so?”

 

He hummed against your throat.

 

“Do tell me about those ideas,” you purred. “I just love to be helpful.”

 

You felt him grin before he gave your neck a sharp little bite. “Let's get outta here, dove.”

 

Helping you to your feet, he took your hand and pulled you away from the party to the sounds of whoops and catcalls. You were sure you'd heard Arat yell _finally_.

 

“Your place or mine?”

 

“How about a free wall,” you breathed. “I don't think I can wait until we've reached either of our rooms.”

 

Simon jerked to a halt as if he'd been electrocuted before turning towards you with a dark look in his eyes, shoving you into a smaller corridor where he pressed you face first against the wall just barely out of sight from anyone who came down the main hall.

 

“This what'cha want, dove?”  he rasped as he dragged his hands up the back of your thighs, squeezing your arse before pulling down your underwear.

 

“Yes,” you hissed as you braced yourself against the wall and stepped out of your knickers.

 

Kicking your legs apart, he crowded against you as you heard the sound of a zipper being undone, making you whimper.

 

“Simon?”

 

“Yeah?”

 

“Leave the mask on.”

 

Simon sucked in a sharp breath at your request but a glance over your shoulder confirmed that he'd pushed the mask back down. You shivered pleasantly. There was something indescribably sexy about being fucked by someone whose face you couldn't see even if you knew exactly who was beneath it.

 

His proximity and small touches had served to fire you up all night and so when he brushed his fingers over your slit, they came back wet.

 

“Would'cha look at this,” he said, sounding muffled, “all ready for me, are ya?”

 

You moaned and arched your back, wordlessly begging for more. When you felt him drag his hard cock across your cunt, coating himself with your slick, you pushed your arse out even further.

 

“So desperate,” he rasped. “D'yer always behave like a bitch in heat or has it been too long since you've been fucked?”

 

“God,” you groaned.

 

He chuckled. “Don't worry, dove, Simon's gonna give it to ya. You're gonna get it good.”

 

And with that he guided his dick into you. Moaning, you rolled your hips, taking him deeper as he kept pushing.

 

“That's it,” he murmured, “take my cock like a good little slut.”

 

You bit your lip at the demeaning name. It wasn't really your style but hearing it in Simon's deep voice while his throbbing length parted your folds made you whimper with need.

 

When he was seated, he put one arm around your waist as the other hand tangled in your hair, tilting your head until your back was bowed and your arse pushed out as far as possible while still keeping you on your feet.

 

“What a pretty sight yer are,” he stated as he began to thrust.

 

Normally, Simon was almost a foot taller than you but your heels made it easier for him to take you in this position, though his bent knees were still brushing the insides of your thighs with each pump of his hips.

 

His hard length sawing in and out of you had you moaning in no time at all. He stretched your folds almost to the point of pain but you were getting more used to his intrusion by the minute as your walls adjusted to his girth. Why on earth had you waited so long to let him have you? He felt amazing inside you.

 

You braced yourself as much as possible in order to keep still for him as he brutally snapped his hips. His groin hitting your arse echoed through the corridor and you were thankful that the music was loud enough to drown out the slapping sound of your coupling. Your thighs were starting to shake from the strain of balancing on high heels while being screwed into next week.

 

Simon was panting harshly as he took you tirelessly. “C'mon, dove, you're not caving in on me already, are ya? Keep those legs steady.”

 

He increased his pace as you mewled from the way he was stroking your pulsing cunt, feeding the ball of heat in your belly. Already, you were desperate to cum. You could tell it was gonna be a good one. The precarious position he held you in made it impossible to free one hand for rubbing your engorged clit. You wanted that added friction but, at the same time, you weren't willing to have him stop since the way he was dominating you right now did funny things to you. Also, he was hitting you in such a delicious angle that you'd gladly have stayed like this forever.

 

Simon moaned as he jerked you back against his thrusts, bottoming out with every stroke which made you tighten around him. Sweat was sliding down your spine, dampening the dress and making it stick to your skin underneath the heavy cape. You whimpered pitifully as the feeling of being stuffed with cock sent shocks through your body.

 

Suddenly, you heard voices coming nearer and you stiffened automatically, clenching around the hard length inside of you, which caused Simon to go even faster, apparently unconcerned with the threat of being discovered. A couple whose names you couldn't recall stopped abruptly when they saw you bent over like a common whore. You felt Simon twitch inside you and realised that he was getting off on being watched.

 

Not slowing down in the slightest, he kept at it. The couple exchanged an uncertain glance before the dude motioned for his girl to get on her knees as he unzipped his pants while his eyes were glued to you taking Simon's cock. Her back was towards you as she did like she was told. It wasn't long before she started to bob her head and the unmistakable sounds of her sucking his dick reached you.

 

Meanwhile, Simon was rocking into you undeterred. Your cunt was beginning to flutter around him as he kept rubbing your walls with his cock. Watching the dude's hand fisting her hair in order to dictate speed and depth while you were being filled over and over again had heat racing through your veins. You moaned as the first pulses of your approaching orgasm made your cunt quiver. Gurgling sounds of her deepthroating him caused you to moan as Simon tightened his hold on your hair.

 

Just before the stranger spilled into her mouth with a strangled grunt, you came hard, spasming around Simon's dick. It felt as though your climax was prolonged by hearing her slurp as she swallowed his cum.

 

Whether it was you clenching down on him while he'd fucked you through your peak or having the pair next to you get off on your coupling, you didn't know but one minute Simon had been riding you mercilessly and the next he'd slammed into you before urgently pulling out and coming all over your arse and thighs.

 

“Leave,” he ordered in a breathless growl making your surprise guests scramble to do his bidding.

 

You slowly got your bearings and gingerly straightened up even though your legs were threatening to give out. Simon's hands on your waist steadied you.

 

Bringing his face to your neck - now sans mask - he murmured, “Your room or mine?”

 

Laughing shakily, you replied, “Haven’t had enough yet?”

 

“The night is still long.”

 

It sounded like a promise.

 


	2. Desire

**Summary for the Chapter:**

> Having had your eye on Simon for a while, you decide it's time to seduce the man.
> 
> Warnings: flirting/innuendos, dirty talk, mutual masturbation, dominant Simon, fellatio, deepthroating, cum swallowing, cunnilingus, fingering, no penetrative sex

**Notes for the Chapter:**

> This is written specifically as a thank you to my beta, [Heeley](https://archiveofourown.org/users/Heeley/pseuds/Heeley), for having my back during Kinktober.

**Day 17 of Kinktober:** **Masturbation** | **Seduction** | ~~Collaring~~ | ~~Orgasm Denial~~

* * *

 

 

After lighting the last candle, you looked around your small room, making sure everything was perfect before taking the strawberries out of the mini fridge and set them next to the fondue dish in which the chocolate was already melting. After pouring two glasses of red wine, you were ready.

As you waited for your guest to arrive, you debated how to present yourself. Maybe draped over the armchair? Or lying sideways on the bed? Or maybe leaning back against the dresser? Or should you give him a view of your backless top right when he comes in?

Deciding it would make you look most at ease if you leaned back against the dresser - masking the butterflies in your belly - you checked your watch and got in position. He should be here any second now.

You perked up at the sound of knocking. Speak of the devil.

“It's open,” you called, licking your lips in anticipation.

The door opened and Simon appeared, looking delectable in his tight-fitting black jeans and a white t-shirt over a dark blue suit jacket. 

“Hi,” you breathed.

He grinned widely. “Evenin’, dove. May I come in?”

“If you dare,” you teased.

“Oh, I dare,” he said firmly as he let his eyes rake over your form.

The blatant hunger in his eyes made your mouth go dry and you involuntarily rubbed your thighs together. A detail that didn't go unnoticed, earning you a smouldering look accompanied by a diabolical smirk that made the ends of his moustache twitch.

Already, you felt the undeniable urge to jump him.

“See somethin’ yer like?”

“You could say that,” you said as you strolled towards the coffee table with an exaggerated sway to your hips.

You could practically feel his eyes boring into your bare back. Smiling to yourself before you shot him a look over your shoulder, you motioned for him to take a seat.

“Wine?”

“Are yer tryin’ to get me drunk?”

“Perhaps,” you said, smirking at him. “Would that offend you?”

“Hell, no,” he exclaimed. “Go right ahead. Feel free to take advantage of me anytime, beautiful.”

“I'll remind you of tha--” 

“Then again, you've lured me to your bedroom and lit a ton of candles while lookin’ good enough to eat, so I guess yer don't need any encouragement, do ya?

“Damn, you saw right through my evil plan,” you said with a dramatic sigh, leaning in as you handed him the glass. “Cheers.”

“Cheers.”

You watched him over the rim of your wine glass, biting your lip at the way his Adam's apple bobbed as you felt a tingle in your belly. How was it that everything about this man turned you on?

“I hope you like strawberries,” you said, as you took one and dipped it into the melted chocolate.

“Why,” he drawled playfully, “I happen to love strawberries.”

“Good,” you purred as you lifted a particularly juicy one to his lips. “Open up.”

“Ain’t that my line, dove?” Simon replied with a filthy grin before complying.

He slowly took the entire fruit into his mouth, sucking on your fingertips before you could let go. You swallowed thickly at the feeling of his silky tongue, thinking of other places you'd like him to lick.

“I don't know, just give it a try later and see what happens.”

You saw his eyes darken at the prospect of getting you to blow him and it made you smile lasciviously as you dipped another strawberry into the chocolate. Bringing it towards your mouth, you subtly arched your back as you slowly slid it halfway into your mouth, deliberately coating your lips in chocolate as you bit into it. Making a show of closing your eyes at the decadent taste, you moaned around the fruit before swallowing the rest of it. Looking up at Simon from under lowered lashes, you licked your lips, delighting in the way his eyes were fixed onto your tongue before slipping your fingers into your mouth. You made sure to suck noisily as you cleaned them, allowing your tongue to snake out every so often before letting go with a pop while forming an exaggerated O with your lips.

A covert glance downwards let you know that Simon appreciated the show, judging by the obvious bulge that was tenting his jeans.

Heat pooled in your knickers at the sight. Sweet Lord Almighty, you wanted his hands on your naked skin so badly.

“So, dove…”

“Yeah?”

“How much do yer wanna finish those strawberries?”

“Why?” you breathed, cocking your head at him. “Got a better idea?”

Keeping eye-contact with you, he reached down to rub his bulge. “I've got a lot of ideas on how to spend our time more pleasurably.”

“Do tell,” you said breathlessly.

Your eyes were glued to the way he grabbed himself.

“Oh, yer like that, do ya?”

You hummed low in your throat. 

“Do yer wanna watch?”

Exhaling sharply as a blush rose to your cheeks, you nodded mutely. The sound of his zipper being undone sent a shiver down your spine and made your nipples harden underneath the thin material of your top. You weren't wearing a bra due to it being backless and so Simon was instantly alerted to your arousal, drawing a husky laugh from him as he freed his hard cock from his jeans.

He was long and thick, leaning slightly to the right. The prominent veins made you feel faint as he slowly fisted his dick. With each stroke, the tip got a little more flushed as pre-cum made it look all shiny and delicious.

You licked your suddenly dry lips as you began to pant at the show he was giving you. Without making a conscious decision, your hands reached up to rub your nipples through the top while you clenched your thighs together.

“Why don't'cha undress for me, dove? Gimme something to look at.”

Wordlessly, you obeyed and got naked, not taking your eyes off of his cock for longer than necessary.

“Move the chair around to face me and then hook your legs over the arms, so I can look at that pretty pussy gettin’ all wet and juicy just for me.”

An audible whimper escaped you as you did as you were told. With your legs spread open, you watched him zero in on your flushed cunt as his hand sped up and a groan escaped him.

Pinching your nipples as wetness began to trickle out of your cunt, you undulated your hips to the pace of his hand.

“Rub your clit,” he commanded in a throaty voice that was full of grit.

Slowly, you slid a hand down your stomach to the apex of your thighs. Spreading your middle and forefinger in a V, you teasingly stroked them over your swollen folds on either side of where you wanted it most. Simon's eyes were wide open and only focused on your glistening core as he bucked into his hand. A ragged moan from him accompanied your fingers finally touching your nub.

Leaning towards you, he let go of his dick and reached out to slide his hand up and down your slit a few times before stuffing two long fingers into your cunt, sending a shockwave through you at the unexpected fullness. Simon grinned up at you when the lewd noises of his digits pumping into your overflowing hole echoed through the room, carrying with it the scent of your arousal. You were meeting every push of his hand while you kept paying attention to your swollen clit. He made a come hither motion that dragged his blunt nails across your g-spot, which had you moaning loudly as you furiously rubbed yourself. 

Pulling back, he held his hand up in front of your face, spreading his fingers to show you that they were coated in your abundant juices before he took a hold of his dick again.

Simon smirked at your expression.

“To ease the friction,” he explained blithely as he covered his cock in your slick wetness.

“God,” you sobbed breathlessly.

“God ain't listening, it's my name you'll need to chant,” he growled, fisting himself with lewd squelching sounds. “Now, finger yourself.”

You obeyed at once. One hand kept rubbing your tingling clit while the other moved lower to breach your entrance. Mewling from the relief of being filled again, you kept your eyes transfixed on Simon angrily jerking himself off as he watched you take one, then two, then three of your fingers. Your hips were raising to accept your digits as deep as they would go while Simon was breathing hoarsely as his dick began to twitch.

Letting go of himself, he stood up and stepped closer to you, motioning for you to remove your legs from the arms of the chair and sit normally while holding his cock steady with a firm grip around the base as he placed his other hand at the back of your head, pulling you forwards until his tip kissed your lips.

Grinning at you mischievously, he echoed your earlier sentiment, “Open up.”

Your heart skipped a beat as you snaked your tongue out to lick across the head, tasting his salty pre-cum. Applying pressure to the back of your head, he thrust his hips forward until you took him into your mouth. Suckling on the fat, mushroom tip, you kept pleasuring yourself as he pushed his length into you. You hollowed your cheeks as you sucked him in, gurgling around his iron hard member when he hit the back of your throat.

“C'mon,” he panted, “open wide. You're gonna have to swallow all of my dick or I won't let yer cum!”

His words made you mewl as you stretched your lips as far as possible and tilted your head a little more so he'd have easier access to your throat. Simon promptly forced himself further as you gagged and swallowed noisily around him. Drool was running down your chin as he began to shallowly thrust, still trying to hilt himself. With every roll of his hips, he slid deeper until your nose was finally pressed into the dark curls at his groin.

Petting your hair, he stated, “Yer look gorgeous with your mouth wrapped around my dick, takin’ me like a pro.”

Despite his words, you were choking around him as he cut off your airflow. Slapping his hip to signal for him to pull back, you made a noise of protest around the cock in your mouth.

“Stop makin’ such a fuss, just breathe through your nose.”

He held you there a few seconds longer before he ever so slowly pulled back. Once he'd dislodged from your throat, you sucked in greedy breaths around him.

“There that wasn't so bad, was it?” he asked rhetorically as he stilled with only his tip still past your lips, keeping you exactly where he wanted you with the hand tangled in your hair. “Again.”

And with that he pushed forward while pulling your face towards his crotch, making your eyes widen when he slipped into your throat once more.

Maybe you shouldn't be turned on by his assertive manner but oh well.

Screwing your eyes shut, you focused on getting enough air into your lungs as Simon moved his hips in long, deep strokes. He had his head thrown back, the tendons in his neck straining as he grunted from the effort of seeking his pleasure. You were deliberately swallowing around him to heighten the friction for him.

Obviously, it was working.

“I'm gonna cum in your mouth and you're gonna drink every last drop, understood?”

Humming around him and reaching a hand out to fondle his heavy balls was what did it.

With a strangled shout, he spilled down your throat before drawing back only far enough to leave his twitching dick lying on your tongue as you sucked harder on him, milking him for all he was worth. Simon cupped the sides of your face as he slowed down until he became too sensitive for your attentions. When he pulled back, you let go of him with an audible pop, making him grin as you pointedly gulped while looking up at him.

“Liked swallowin’ my cum, did ya?”

“Yeah,” you admitted hoarsely.

“What a perfect little cocksucker yer are, dove,” he praised. “How ‘bout I return the favour, huh?”

Eagerly, you nodded your head. “Yes, please!”

With a chuckle, he knelt down in front of you, sliding his hands up the insides of your thighs to open your legs for him. Shuffling closer, he spread your lips apart with his thumbs.

“Such a pretty pussy,” he murmured with his lips so close to your cunt that you could feel his hot breath wash over your clit while the ends of his moustache tickled your skin, making you instinctively want to press your legs together. “Nuh-uh, keep'em spread for me, dove, or yer won't get your treat.”

Simon came even closer and threw your legs over his shoulders.

Your back arched as he dragged his tongue through your slit from opening to clit before drawing back and noisily tasting the essence left on his tongue. Looking at him with half-lidded eyes, you panted as you waited for him to continue.

“Delicious,” he said with a smack of his lips before diving in.

As he sucked your clit into his mouth, your hands flew to the armrests, digging your nails in while he pushed two fingers into your needy hole and began to fuck you with them. Lashing his tongue against your pulsing nub, he reached up with his free hand to twist a nipple while forcing a third finger into your cunt. You were more than ready for the stretch. Already, you were convulsing in you seat from the mind-blowing friction he provided for you. Your moans and whimpers mixed with the wet sound of him screwing his digits deep into your hole while he circled your clit with his tongue and alternated between each nipple.

And people claimed men weren't able to multitask…

That ball of heat in your abdomen that had been steadily coiling tighter and tighter ever since Simon had entered your room was about to explode, you could feel it. Your toes curled as you canted your hips towards him, seeking relief but not being able to reach it quite yet. Simon looked up at you while his mouth was pressed to your mound and then massaged your g-spot with his fingers as he scraped his teeth across your clit, making tears shoot into your eyes as you came crashing down. All the muscles in your body tensed as you threw your head back and screamed bloody murder.

When you'd calmed down, Simon was softly lapping at your clit, while stroking your side and holding his fingers immobile in your still clenching cunt, letting you ride out your orgasm. Weakly, you pushed against his bicep, motioning for him to stop sucking on you as that had you spasming painfully.

With a last firm suck, he sat back on his haunches. Drops of your essence hung like glistening dew in his moustache as he licked his fingers clean of your cum.

Raising an eyebrow at your flushed appearance, he grabbed the bowl from the table behind you and held it up towards you.

“Strawberries?”

 


End file.
